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Mansion vacation rentals in Siesta Key

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Top-rated mansion rentals in Siesta Key

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Home in Holmes Beach

4.87 out of 5 average rating, 103 reviews

New Golf cart + 4bd/3b w pool/2100 sq ft home

Urban Oasis is a privately owned 2100 sq ft 4 bd, 3 bth on Anna Maria Island. 4 minute walk on a quiet residential street to walk to the beach.This home features grey blue hues, coastal furniture, driftwood accents, themed rooms and designer accents. A brand new 2024 6 str golf cart is included in your rental as well as a premium linen service including all towels and linens. Urban Oasis is truly a turnkey Vacation Rental! We also have a second property, Urban Oasis Too, if you like our style!

Home in Bradenton

4.97 out of 5 average rating, 117 reviews

Near downtown! Saltwater Pool! HOT TUB! Games!

Beach! River! Heated Saltwater Pool! Hot Tub! Your tropical beach vacation awaits! Prime location in proximity to local restaurants, attractions & sparkling waters. Nathan Hejl Interior Designer has updated this spacious 5BR/3.5BA vacation oasis to blend luxurious furniture & finishes w/ a barefoot, tropical vibe. Located in Historic River District in W Bradenton, walking distance to Manatee River, 2mi to Bradenton Convention & only 8mi to the famous Anna Maria Island beaches, 20mi to #1 Siesta

Home in Bradenton

4.87 out of 5 average rating, 118 reviews

IMG golf & close to AMI- Ocean View | Slt Wtr Pool

Welcome to The Beachview @ Bayside in beautiful Bradenton, Florida—a true slice of paradise with stunning views of the inner coastal waterway, Longboat Key, and Anna Maria Island! This spacious beach retreat offers 3 main-level bedrooms and an exclusive Master/Family Suite upstairs, providing the perfect setup for families or groups of friends. Comfort & Relaxation Await Each of the three main bedrooms features a private deck, ideal for sipping your morning coffee or enjoying a sunset cockta

Home in Holmes Beach

4.97 out of 5 average rating, 128 reviews

Twin Palms: Big House Steps to Beach w/Lush Pool

Twin Palms is home to NY Times best-selling food writer and chef and her tech husband. Infant/kid/pet-friendly (to 35 lbs) in a great location 5 min. walk to the beach. Private lagoon-style *heated* pool amid lush landscaping with gorgeous rock waterfall. Fully updated kitchen, 60-inch Sony HDTV, 55'' Samsung Frame TV, Italian leather reclining sofas, BBQ, beach gear, updated bathrooms, three king bedrooms. Classic Florida one-level home - no stairs. Managed directly by owners. No crazy fees!

Home in Sarasota

4.96 out of 5 average rating, 143 reviews

La Hacienda / heated pool, hot tub, 6mi to beach

Experience the allure of La Hacienda, a charming rental with a warm Southwestern-inspired interior with unique touches. This 4-bedroom, 2-bath home features a spacious living room with comfortable seating and multiple smart TVs. The private backyard awaits with a heated pool, hot tub, and outdoor kitchen for ultimate relaxation and entertainment. Located near downtown, you'll have easy access to beaches and dining. Indulge in the perfect blend of chillin', grillin' and sippin' at La Hacienda!

Home in Bradenton Beach

4.97 out of 5 average rating, 159 reviews

Welcoming Back Guest: Jan 1, 2025!

Less than a 2 minute WALK from the white sand beaches of the Gulf, this 4 BR home comfortably sleeps 8. With large bedrooms & a spacious floor plan (the kitchen, dining and living rooms flow together), the house is perfect for families. The bedrooms are split 2+2 & paired with a bathroom on opposite ends of the house (a pocket door adds privacy). Private heated salt water pool sits amidst the lush tropical yard. Hop on the free A/C'ed trolley and explore Florida's gorgeous Anna Maria Island.

Home in Sarasota

4.97 out of 5 average rating, 152 reviews

LUXE home 6mi to Siesta w/ incredible pool area!

Welcome to The Palmieri - the ideal Sarasota family vacation destination! Minutes from DT, Siesta & Lido beach, our beautifully styled home features an incredible backyard with a heated saltwater pool, hot tub, fire pit, playland, and a shaded lounge. Spacious and open inside, with a fully equipped kitchen, and all the cozy feels of home. The finished garage houses beach supplies for your convenience, and thoughtful touches throughout combine comfort & luxury for an unforgettable experience.

Home in Sarasota

4.94 out of 5 average rating, 186 reviews

Modern, Bright Downtown SRQ A-Frame West of Trail

Enjoy this bright, newly renovated unique pool home on a street with mostly waterfront homes featuring 4 beds & 3 baths, office area options, loft reading nook, Bosch appliances, bedroom skylights, artful light fixtures and fully fenced with heated pool. Central to & minutes from Siesta Key, St. Armand's Circle/Lido Key, downtown and more. Walk to the Sarasota Arts Museum, grocery, Southside and downtown Restaurants & shops, Selby Botanical Gardens, Bayfront Park, & Marina Jack.

Home in Bradenton

5 out of 5 average rating, 118 reviews

HTDPool~2KingSuites~3BathRm~FIREpit~Airhockey~CRIB

We have been very fortunate and our home has not been affected by hurricane Helene. Our home is available for rent now. ▪️2 Game Rooms ▪️2KingSuites ▪️7 miles to Beach ▪️Blackout curtains ▪️BabyMonitor▪️Crib/Pack N Play/HighChair ▪️RokuTV’s▪️Self Checkin ▪️AirHockey ▪️Grill ▪️FirePit ▪️Washer/Dryer ▪️Coffee Bar▪️Cable ⭐️Short Checkout List⭐️ Book your family's fun beach vacation TODAY.🏖️ And create memories for a lifetime!😀 Ask us about any special offers!⛱️👌

Rental unit in Siesta Key

5 out of 5 average rating, 22 reviews

Coastal Luxury Penthouse

This luxury Penthouse condo is in the heart of Siesta Key Village. There is no other property in Siesta Key that can compare to this one in location, amenities, and size that can not only house your entire party, it provides every piece of luxury needed to make your trip the most memorable experience. This 2 floor, 4 Bedroom, 3.5 bathroom Penthouse is equipped with a private entrance elevator, 2 car garage, private rooftop terrace, and 6 exterior balconies to enjoy.

Home in Bradenton

4.91 out of 5 average rating, 349 reviews

Palm Retreat: #1 Top Rated Rental of Bradenton/AMI

Enjoy Florida sun in a stunning, newly renovated 4/2 pool home! We have provided almost everything we could think of including five 4k TVs w/ Netflix and cable, wifi, heated (optional) salt water pool w/ 7' privacy fencing, adult bikes, beach gear, Pack & Play, office, board games, relaxing lounge chairs, stocked kitchen, washer & dryer, garage parking, dog crate, all in a quiet and safe neighborhood. Oh, and of course it's just 5 miles to world renowned beaches.

Home in Sarasota

4.94 out of 5 average rating, 150 reviews

Wood Street Retreat 4/2 Near Beaches & Downtown

Discover elegance in this centrally located Sarasota gem, featuring four bedrooms and two bathrooms to accommodate up to eight guests. Enjoy a laid-back vibe while lounging at Sarasota's beaches or immersing yourself in local attractions. Siesta Beach and Lido Beach are within easy reach at 7.6 and 6.4 miles respectively. Rest easy knowing commitment to cleanliness aligns with your travel priorities. Your serene vacation awaits in this beautifully adorned home!

Vacation rentals for every style

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Popular amenities for Siesta Key mansion rentals

Free parking on premises

Air conditioning

Luxury mansion rentals

Home in Bradenton

4.9 out of 5 average rating, 109 reviews

4BR Htd Pool- IMG Acad Golf View/16ppl/Near Beach

Home in Anna Maria

5 out of 5 average rating, 22 reviews

Veselka - Canal front w private heated pool & dock

Home in Holmes Beach

5 out of 5 average rating, 23 reviews

Sunkissed & Salty: Guest Favorite! Prime Island L

Home in Siesta Key

4.83 out of 5 average rating, 58 reviews

A Family Island Treasure

Home in Sarasota

5 out of 5 average rating, 48 reviews

Luxury villa near Siesta - heated, screened pool

Home in Sarasota

5 out of 5 average rating, 42 reviews

Family Fun House near Siesta Key Beach

Home in Anna Maria

5 out of 5 average rating, 22 reviews

༄ Sunset Shore on Anna Maria Island ༄

Villa in Sarasota

4.79 out of 5 average rating, 33 reviews

Relaxation awaits in this bohemian inspired villa

Pet-friendly mansion rentals

Home in Sarasota

4.82 out of 5 average rating, 161 reviews

☀ Pet and Family Friendly Home with Pool ☀

Home in Downtown Sarasota

5 out of 5 average rating, 28 reviews

Coastal Contemporary Pool Home

Home in Bradenton

4.86 out of 5 average rating, 146 reviews

Resort Style Backyard Oasis w/Heated Pool/Tiki Bar

Home in Bradenton

4.94 out of 5 average rating, 119 reviews

Spa & Pool+By The River+Near Beaches+Gameroom

Home in Sarasota

5 out of 5 average rating, 30 reviews

Family friendly with large pool

Home in Sarasota

4.82 out of 5 average rating, 213 reviews

Home away from home mins to Beach! Special deals!

Home in Sarasota

4.97 out of 5 average rating, 70 reviews

Renovated Ranch near Downtown Sarasota and Siesta

Home in Indian Beach-Sapphire Shores

5 out of 5 average rating, 16 reviews

Private Resort

Mansion rentals with a pool

Home in Bradenton

5 out of 5 average rating, 10 reviews

Sunshine Family Paradise With Heated Pool & King B

Home in Sarasota

4.95 out of 5 average rating, 39 reviews

Luxurious Summer Family Oasis w/ Private Pool!

Home in Sarasota

4.91 out of 5 average rating, 47 reviews

Hideaway House Boho Retreat Pool Spa Siesta 3.5m

Home in Bradenton

4.97 out of 5 average rating, 29 reviews

Pool, putting green, pickleball, tiki bar, hot tub

Home in Sarasota

4.88 out of 5 average rating, 58 reviews

Olive Tree Oasis- 5/2 with Hot Tub & Heated Pool

Home in Sarasota

4.9 out of 5 average rating, 62 reviews

[The Bay St. Hideaway]Private Swimming Pool& Patio

Home in Sarasota

4.97 out of 5 average rating, 69 reviews

Minutes to Siesta Key, heated pool & tiki on water

Home in Sarasota

5 out of 5 average rating, 23 reviews

Urban Oasis, Pool, 6mi>Beach

Destinations to explore